Gel-forming polypeptide derivatives

The invention relates to N-terminal Fmoc-protected peptide combinations that form gels in water and diverse organic solvents, and whose representative overall formulas are: (I), where R.sup.1 is CH.sub.3, CH.sub.2 --CH(CH.sub.3).sub.3, CH(CH.sub.3)CH.sub.2 CH.sub.3, R.sup.2 is H, CH.sub.3, CH.sub.2 OH, (CH.sub.2).sub.n --COOH, (CH.sub.2)4--NH--CO--OCH.sub.2 C.sub.6 H.sub.5, R.sup.3 is dipeptide remainder, m is 0 or 1 and, n is 1 or 2; or (II), where R1 is CH.sub.3, CH.sub.2 --CH(CH.sub.3)2, or CH(CH.sub.3)CH.sub.2 CH3, R2 is CH2--CH(CH3)2, R3 is H, CH.sub.3, CH.sub.2 OH, (CH.sub.2).sub.n --COOH, or (CH.sub.2)4--NH--CO--OCH.sub.2 C.sub.6 H.sub.5, R.sub.4 is tripeptide remainder, m is 0 or 1 and, n is 1 or 2. These types of peptides form gels in aqueous solutions and are biologically compatible and may be useful for drug delivery, antigen delivery and may be useful as food additives to retard spoilage and act as fillers.

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Claims

1. An F-moc derivatized anionic dipeptide of the general formula: ##STR3## wherein: R1 is selected from the group consisting of CH.sub.2 --CH(CH.sub.3).sub.2 and CH(CH.sub.3)CH.sub.2 CH.sub.3;

R2 is selected from the group consisting of H, CH.sub.3, CH.sub.2 OH, (CH.sub.2).sub.n --COOH, and (CH2).sub.4 --NH--CO--OCH.sub.2 C.sub.6 H.sub.5;
R3 is OH;
m is either 0 or 1; and
n is either 1 or 2.

2. The dipeptide of claim 1 wherein R2 is CH.sub.2 --COOH.

3. The dipeptide of claim 2 wherein R1 is CH.sub.2 --CH(CH.sub.3).sub.2.

4. The dipeptide of claim 2 wherein R2 is CH(CH.sub.3)CH.sub.2 CH.sub.3.

5. An aqueous gel comprising water and 0.1% to 5.0% by weight of the dipeptide of claim 1.

6. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 1.

7. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 2.

8. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 3.

9. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 4.

10. The aqueous gel of claim 5 further comprising an antigen.

11. The aqueous gel of claim 5 further comprising a low molecular weight drug.

12. The aqueous gel of claim 11 wherein the low molecular weight drug is selected from the group consisting of 3,5-dimethyl-1-adamantanamine hydrochloride and 5-methyl-1-adamantanamine 3-carboxylic acid.

13. An F-moc derivatized anionic dipeptide of the general formula: ##STR4## wherein: R1 is selected from the group consisting of CH.sub.3, CH.sub.2 --CH(CH.sub.3).sub.2 and CH(CH.sub.3)CH.sub.2 CH.sub.3;

R2 is selected from the group consisting of CH.sub.2 OH, (CH.sub.2).sub.n --COOH, and (CH2).sub.4 --NH--CO--OCH.sub.2 C.sub.6 H.sub.5;
R3 is OH;
m is either 0 or 1; and
n is either 1 or 2.

14. The dipeptide of claim 13 wherein R2 is CH.sub.2 --COOH.

15. The dipeptide of claim 14 wherein R1 is CH.sub.2 --CH(CH.sub.3).sub.2.

16. The dipeptide of claim 14 wherein R1 is CH.sub.3.

17. The dipeptide of claim 14 wherein R2 is CH(CH.sub.3)CH.sub.2 CH.sub.3.

18. An aqueous gel comprising water and 0.1% to 5.0% by weight of the dipeptide of claim 13.

19. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 13.

20. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 14.

21. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 15.

22. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 15.

23. An aqueous gel comprising water and 0.1% to 1.0% by weight of the dipeptide of claim 17.

24. The aqueous gel of claim 18 further comprising an antigen.

25. The aqueous gel of claim 18 further comprising a low molecular weight drug.

26. The aqueous gel of claim 25 wherein the low molecular weight drug is selected from the group consisting of 3,5-dimethyl-1-adamantanamine hydrochloride and 5-methyl-1-adamantanamine 3-carboxylic acid.

27. A method for making an aqueous gel comprising:

placing a dipeptide of claim 1 in water under conditions to form a gel and allowing the gel to form.

28. A method for making an aqueous gel comprising:

placing a dipeptide of claim 13 in water under conditions to form a gel and allowing the gel to form.
Referenced Cited
U.S. Patent Documents
4758550 July 19, 1988 Cardinaux et al.
5162512 November 10, 1992 King et al.
5214195 May 25, 1993 Kung et al.
5280113 January 18, 1994 Rademacher
5324786 June 28, 1994 Kunz et al.
Patent History
Patent number: 5955434
Type: Grant
Filed: Aug 9, 1996
Date of Patent: Sep 21, 1999
Assignee: Brigham & Women's Hospital (Boston, MA)
Inventors: Paul A. Janmey (Arlington, MA), Rolands Vegners (Riga)
Primary Examiner: Cecilia J. Tsang
Assistant Examiner: David Lukton
Law Firm: Wolf, Greenfield & Sacks, P.C.
Application Number: 8/693,215
Classifications
Current U.S. Class: 514/19; Of Amino Group (530/337)
International Classification: A61K 3805;